Sodium hydride → 3-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

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Reaction Steps

3-Chloro-5-methoxypyridazin-4-ol (0.20 g) was dissolved in DMF (3.1 mL), NaH (0.0595 g, 60%, in oil) and tetrabutylammoniumiodide (0.0916 g) were added at 0° C., and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added (bromomethyl)cyclopropane (0.138 mL) at 0° C., and the mixture was stirred at 0° C. for 2.5 hr, at room temperature for 1 day and at 40° C. for 20 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (0.136 g).

Provenance & Evidence